4-Methylmorpholine → ethyl 5-(1-(4-chlorophenyl)-1-(4-(methylsulfonamido)-1H-indazol-1-yl)propyl)-1,2,4-oxadiazole-3-carboxylate

HRID 1477899Notes

Reaction equation

HRID 1477899 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:11]([C:21]1[O:25][N:24]=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:22]=1)([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH2:12][CH3:13].CN1CCOCC1.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]([C:21]2[O:25][N:24]=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:22]=2)([N:6]2[C:7]3[C:3](=[C:2]([NH:1][S:39]([CH3:38])(=[O:41])=[O:40])[CH:10]=[CH:9][CH:8]=3)[CH:4]=[N:5]2)[CH2:12][CH3:13])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 70563925ethyl 5-(1-(4-amino-1H-indazol-1-yl)-1-(4-chlorophenyl)propyl)-1,2,4-oxadiazole-3-carboxylate

Product 1

HCID 70563586ethyl 5-(1-(4-chlorophenyl)-1-(4-(methylsulfonamido)-1H-indazol-1-yl)propyl)-1,2,4-oxadiazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Step D above (0.080 g, 0.17 mmol) and N-methylmorpholine (0.035 g, 0.35 mmol) in DCM (1.0 mL) was added methanesulfonyl chloride (0.019 g, 0.17 mmol) at 0° C. After stirring at RT for 30 min, the reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with dioxane/water, acidified with TFA, and purified directly on RP-HPLC to give the title compound. LC/MS m/z=504.1 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe resulting residue was diluted with dioxane/water
  3. custompurified directly on RP-HPLC

Sources & evidence

ORD record
ord-bca892393c844985a7588db2a423623e
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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